Over The Desk
by General-Fullbuster
Summary: Pacifica is yet again in trouble with her boss Dipper, and he intends to punish her thoroughly. Warning, this story contains lemon and spanking.


**A/N: Warning, this story contains spanking and rough sex. Just so no one gets confused, this story is intended to be role play between the characters. This is NOT a rape. When I write a rape fic, you'll know...**

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Pacifica typed away at her computer, trying to keep her mind focused on her current task. It was so easy to want to just slip into a daydream and just leave this boring work behind. But sadly she couldn't afford to. She needed to set up the meeting with Cabbage Co (which was a horrible name for a company by the way) before the end of the day. Her boss was pretty stern, and he'd be pissed if it wasn't done by clock out time.

"Ms. Northwest."

She jumped slightly when she heard the voice come from the intercom on her desk. It was her boss, and from his tone he didn't sound very pleased. She hesitantly reached forward and pressed the button on the intercom. "Yes sir?" She asked, annoyance clear in her voice. She wasn't sure what she did, but she was sure it wasn't good.

"Can you come to my office? We need to have a discussion."

She felt a chill go up her spine. She was in trouble. Deep trouble. "Yes sir. I'll be in shortly." She let go of the button and let out a breath. Today was certainly going to be interesting. She stood up and began making her way to his office, her high heels clicking against the floor as she walked. Eventually she made it to her boss' rather large double doors.

She did a mental checklist of herself. She was wearing a purple blouse that hugged her tightly and showed off more than a bit of cleavage, along with a black pencil skirt that was short enough to show off her lovely legs which were further complimented by her garnet stockings. She looked stunning as always. Whether that would be an advantage or disadvantage remained to be seen.

She sighed and then pushed her way through the doors. The sight that greeted her was just as chilling as ever. Dipper Pines sat behind his desk skimming through one of his old mystery books. "You wanted to see me Mr. Pines?" She asked crossing her arms.

She really should have hated him. He'd come in with his genius level intellect and swiftly rose through the ranks of the Northwest company. Her father had been incredibly impressed with him from the start. He'd seen someone who could further boost the company's success. It had been the first time she had heard her father say someone might be better at him than something.

And it was just infuriating when he'd put him in charge of the company over her. Here was this nobody who'd come from nowhere, sitting in what was practically her throne. And here she was, as nothing but his secretary. An admittedly well paid secretary, but a secretary nonetheless.

But despite her hatred of him, she still couldn't help but respect him. He'd run this place better than she ever could. "I don't believe I heard a knock on my door before you entered Ms. Northwest." Dipper said not even bothering to look up from his book.

"Sorry sir. I thought it was urgent." She spat.

"It is." He said setting the book down. "But that's not an excuse to forget your manners. Now come have a seat. We have a very important matter to discuss." The blonde walked forward, purposely swaying her hips as she approached him. He nodded towards the chair in front of his desk, and she took a seat. Then he pulled out a piece of paper and set it on the desk before sliding it in front of her. "Tell me what this is."

She looked over the sheet of paper. It was a letter. A letter she had written to one of their business partners yesterday. "A letter." She answered smirking.

"Very observant." He said smirking back. "Now, read it." Pacifica silently, and a bit nervously, began reading over the piece of paper, and the further she went on, the more she felt her breath get caught in her throat. "How many?"

She knew what he was talking about, but played dumb anyway. "How many what sir?"

"Don't be cheeky. How many typos are in that letter?" He asked.

"Three…"

"Four…" He corrected.

"Fine, I'll retype-"

Dipper held his hand up. "No. I already cleaned up the typos and sent the letter. We're not here to talk about correcting the letter. We're here to discuss correcting your work ethic. This has been going on long enough, and I think some type of repercussion is on order."

Pacifica felt her heartrate begin to sky rocket. "That isn't fair, I -"

"What's unfair about it? If you haven't straightened up by now then I doubt you'll start anytime soon." He said laying back in his chair. "You keep screwing up, so you have to be punished. Or would you rather be fired?"

"No sir…" She responded through gritted teeth.

"So what do you think I should do?"

"I think… that you should punish me as you see fit."

Dipper smiled. "I'll do just that." He pulled the drawer to his desk open, and Pacifica felt her heart skip a beat as he pulled out a thin wooden cane. "Stand up, move the chair to the side, bend over the desk." He ordered as he rose to his feet.

"Dipper I-"

"Every second you're not over that desk will only make things worse." Pacifica flinched, then quickly stood up and put her chair to the side. She slowly began to bend over the front of the desk, only to be pushed down the rest of the way. "You're a very undisciplined girl, you know that? You're father spoiled you rotten and you turned into a brat with no real sense of work."

Pacifica scowled as he placed his hand against the seat of her skirt. "I know sir…" She mumbled. He was right. Her father had spoiled her. Over the past year Dipper had been doing a good job of caning that uppity attitude out of her, but clearly he felt there was still more work to do.

He rubbed his hand over her rear, caressing his soon to be target. "How many do you think you should get?" He asked. She knew there was no point in answering. Any number she gave would be insufficient. "Let's see. You had four typos. Why don't we go with… four for each one. That adds up to an even sixteen. How does that sound?" He said giving her rear a pinch.

She paled. Sixteen? Would she really be able to take that many? The most she'd ever been given before was twelve, and that was only once. Well, she would have to find out. "Good sir."

Dipper backed up and then raised the cane. "Count and thank me for each one. You move out of position or forget to count, and the stroke won't count. Understand?"

"Yes sir."

THWACK!"

"Uh!" Pacifica balled her fist up as she felt the cane bite into her rear. It felt like a line of fire had been drawn across her butt. She knew from experience that the stinging was not about to die down anytime soon. "One sir, thank you."

THWACK!

"AH!" Another line of fire. She had thought after all this time she might have gotten used to this pain, but Dipper never made it easy for her. "Two sir, thank you."

THWACK!

"OH! Three sir, thank you!"

THWACK!

"OUCH! Four sir, thank you!"

THWACK!

"Five sir, thank you!"

Dipper smiled as he continued to cane the lovely blonde before him. He loved the position that he held over this woman, who had once had a huge degree of control over his life. He loved being able to order her around. To watch as she squirmed under him. He could just imagine the lines forming across her perky firm little rear.

He gave another flick of his hand. THWACK! Pacifica's knees nearly buckled at the last stroke. She clung onto the desk as if for dear life. "Oh… Twelve sir, thank you." She groaned.

Dipper was slightly impressed. The last time she'd gotten to twelve she had been bawling like a baby. This time she was clearly shaken, but still managing to compose herself. Well, that was going to have to change. "I'm removing your skirt." He stated.

Pacifica grew wide eyed. "What…?"

"I don't feel as though this lesson is quite sinking in for you, so you'll take the last six with your skirt up. Do you have any complaints?" He asked with a smirk.

She could feel sweat starting to form on her forehead. This was definitely a first. The skirt may not have been much, but it did offer a little protection. Now she would have none. At twelve strokes she was already on her last leg. Now she had to take six more on the bare? But she didn't really have a choice did she?

"N-No sir."

Dipper nodded, and she turned back around. He grabbed the hem of her skirt, and lifted it upwards. He tucked it in the back of her waistband and then looked over the two well rounded orbs before him. Just as he'd guessed, even over her purple nylon panties you could see there were twelve beautiful crimson red lines going down her cheeks. He reached up and touched them, and she winced. He ran his fingers across them. "Are you ready for the final six?"

"Yes sir…" As if she had any say in it.

He pulled his hand back and lifted the cane once more.

THWACK!

"GAH!"

She looked ready to jump up, but Dipper quickly pressed his hand against her back. "I told you not to move." He reminded. "That one doesn't count. I suggest you get it together or we'll be here all day." Pacifica bit her lip. That had hurt terribly. But he was right. She needed to endure, or else she'd only end up getting more.

THWACK!

"OUCH!" She bucked against the desk, but didn't break position. "T-thirteen sir, thank you." She said with a sob.

THWACK!

"AAHH! F-Fourteen sir, thank you!"

THWACK!

"OH GOD! Fifteen sir, thank you!"

THWACK!

"YEOUCH! Sixteen sir, thank you!"

She panted, thankful the torture had finally come to an end, but stayed over the desk, knowing better than to break position even after the punishment was over. She sniffled, her mascara running down her tear stained face. She had never been caned so harshly before.

Dipper chuckled. "Well, color me impressed. You actually lasted all sixteen. But…" He reached forward and then slid his hands between her legs. Pacifica gasped. "I'm still not completely sure that the lesson stuck, if this is any indication." He said running his fingers over her clit. Her panties were soaking wet.

"No sir, I understand. I've learned my lesson." She managed to grunt out as he began toying with her. Dipper always seemed to know just how to tease her in the worst ways. It was taking all she had to keep herself bent over as his finger continued to push against her sex.

Dipper was clearly having fun riling her up. "I don't believe you. You'll be back in here by the end of the week. But you did take your sixteen like a good little girl, so I'll let you off. Still, I can't leave you like this. You're barely focused when you're not crazy aroused. You'll never get anything done like this. Why don't we clear your head?"

Before she could answer, he reached up and pulled her panties down to her knees, exposing her completely bare bottom. Pacifica could hear the sound of a zipper going down, and then gasped as she suddenly felt something large press against her clit. Dipper slowly moved forward, inching his hardened member into her.

The blonde panted as he speared into her. All the tension from her punishment needed to be let loose, but going slow like this was only building it up even further. She shouldn't have expected anything less though. He'd always loved dragging it out his time with her. She shifted uncomfortable, moving her hips back and forth, until he grabbed them and held her in place.

"Be still." He ordered.

Pacifica did as instructed, not that she could do otherwise while in his grip. Once Dipper finally finished his agonizingly slow thrust into her, he leaned forward until he was next to her ear. "Do you want me to keep going?" He asked.

"Yes sir."

"Then say who you work for."

"You sir."

He pulled back, only to deliver once quick hard thrust. Pacifica grunted, her freshly marked bottom flaring up in pain from the skin on skin contact. "Who do you live for?"

"You sir!"

He thrusted again, earning another grunt from her. "Who do you belong to?"

"You sir!"

Dipper began picking up the pace, going in and out of her with more force. Pacifica winced and grunted. Every thrust into her reminded her of the pain in her rear. But it was also mixed with an undeniable pleasure. Dipper kissed her neck as he continued to ravage her. "Are you enjoying yourself?" He asked.

"Yes sir! Very much sir!" She managed to scream out. "I-I'm going to cum!"

"No you're not." He whispered into her ear. "Not until I do first. Otherwise you'll be getting another sixteen."

Pacifica bit her lip. She knew just how much stamina Dipper had. Between her spanking and his teasing, she wasn't sure she could hold out that long. But she also knew she couldn't take another round with the cane. "Oh god…" She mumbled. "I can't do it…"

"You can and you will." He said before reaching back and pinching her butt. She yelped and lifted her feet, flailing them helplessly in the air. She was held in place by Dipper's body. "Does that hurt?" He asked smugly. "Good. I don't want you feeling too much pleasure. This is still a punishment."

"Feeling thoroughly punished sir! AH!"

Pacifica wasn't sure how long he had continued pulling in and out of her. It could have been minutes, or hours for all she knew. But every second of it was pure agony, and pure bliss. With every movement of Dipper's hips came a wave of pain and pleasure that mixed together to drive her pussy insane.

This was unbearable. If things kept going like this she wasn't going to make it. She clung to the desk, desperately trying to hang on for just a minute or two longer. "Almost there. Almost…" Dipper said. Pacifica was incredibly tight, her pussy clamping down on his member hard. "Almost…" He gave one more powerful thrust into her.

Pacifica cried out as she felt him shooting his seed into her, her body tightening up as she finally allowed herself to cum as well. For those few moments, the pleasure had completely overridden the pain. She felt pure ecstasy. After those moments finished, her body went limp and she collapsed onto the desk.

Both she and Dipper were panting, trying to catch their breaths. Dipper backed up, and Pacifica let out a sigh as he pulled his member out of her, allowing both of their fluids to spill onto the floor. He stood and looked down at his secretary. She certainly looked like a mess right now. Her ass was bright red, and her fluids were spilling down her legs.

He smiled before bringing his hand back and smacking her rear. She grunted. "On your feet." Pacifica stayed down for a few more moments, feeling too tired to comply. He gave her another slap. "Up." He ordered. Pacifica took in a breath before weakly pushing herself up off the desk and up to her feet. "Turn around."

Pacifica slowly turned around and faced him. Dipper reached up and raised her chin before leaning down and planting a kiss on her lips. Pacifica didn't resist and quickly kissed him back. She moaned into the kiss as Dipper began wrapping his arms around her waist. He pulled her closer deepening the kiss.

She noted he tasted like wintergreen. He always kept wintergreen mints on him, on the off chance that his breath stunk before a meeting. After a while he broke the kiss and then released her. "Well, I think we're done here. You're thoroughly punished and clear headed. Now go find a towel, clean up your mess, and get back to work."

"Yes sir." She said as she began to make her way out of the room, legs still wobbling.

Dipper gave her one last hard smack on the ass, which earned a grunt and a shudder up her spine. For a moment she was she felt like she was going to orgasm once more, but somehow she'd held it in. "Hop to it."

"Yes sir."

She quickly made her way out, pulling her panties back up as she did. That had by far been their most intense session yet. She was going to be sleeping on her stomach tonight. Dipper seemed determined to keep on pushing just how far they'd go… not that she was complaining. The stricter he got with her, the harder she came. In fact, maybe she would make another little mess while she was cleaning up his office today.

She smirked. Yeah, that sounded like a good idea.

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 **A/N: Short one shot I wrote for the hell of it.**


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